Diphenylmethylidenehydrazine → HCID 59799038, compound

Participants

Role	Name	HCID	Charge
Reactant	Diphenylmethylidenehydrazine	HCID 79304	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	HCID 57447742	HCID 57447742	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Product	HCID 59799038	HCID 59799038	87%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.39 g, 10.2 mmol) in dry, degassed toluene (100 mL) under nitrogen, then add benzophenone hydrazone (2.00 g, 10.2 mmol), sodium tert-butoxide (1.37 g, 14.3 mmol), BINAP (635 mg, 1.02 mmol) and bis(dibenzylideneacetone)palladium (0) (280 mg, 0.306 mmol). Stir at 100° C. for 8 hr, cool to RT, concentrate and purify (silica gel chromatography, eluting with 95:5 2-methylpentane:EtOAc) to give the title compound (4.2 g, 87%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07981882B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-001b6970d51940bda81ee4f9173a14ad
Source note	uspto-grants-2011_07